Solvent-Controlled and Highly Chemoselective Reduction of α,β-Unsaturated Ketones and Aldehydes.

Herein, we establish two highly efficient reductions of α,β-unsaturated ketones and aldehydes via Raney nickel-catalyzed hydrogenation with distinct chemoselectivity, which is controlled by the solvent. This methodology demonstrates a brilliant result when reducing α,β-unsaturated ketones and aldehydes to ketones or alcohols. High isolated yields were obtained for a series of benzalacetone- and cinnamaldehyde-derived substrates without additional column chromatographic purification. The practicability of the methodology was demonstrated by reducing the natural products and synthesizing the approved drug.